2-Amino-5-fluorobenzoic acid Chemical Properties

Melting point:

181-183 °C(lit.)

Boiling point:

223.67°C (rough estimate)

Density 

1.3021 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

1.86±0.10(Predicted)

form 

Fine Crystalline Powder

color 

Light yellow to light brown

BRN 

2803664

InChI

InChI=1S/C7H6FNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)

InChIKey

FPQMGQZTBWIHDN-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(F)=CC=C1N

CAS DataBase Reference

446-08-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:5-Fluoroanthranilic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Amino-5-fluorobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Used in the synthesis of styrylquinazolinones which are potential anticancer agents.

Uses

2-Amino-5-fluorobenzoic acid is used for the counterselection of TRP1, a commonly used genetic marker in the yeast Saccharoyces Cerevisiae. An antimetabolite for the tryptophan pathway in yeast, and is toxic by virtue of its antimetabolite conversion to 5-Fluorotryptophan. It can be used for the selection of tryptophan auxotroophs.

Definition

ChEBI: An aminobenzoic acid that is anthranilic acid in which the hydrogen at position 5 on the phenyl ring is replaced by fluorine.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 2-amino-5-fluorobenzoic acid from 2-nitro-5-fluorobenzoic acid: 2-nitro-5-fluorobenzoic acid (10 g, 54 mmol) was dissolved in ethanol (100 mL) and 10% Pd/C catalyst (0.5 g) was added. The reaction was stirred at room temperature for 4 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration. The filtrate was concentrated under reduced pressure to give 8.2 g (98% yield) of the white solid product 2-amino-5-fluorobenzoic acid. Product melting point: 142 °C. 1H NMR (DMSO-d6) δ: 6.71 (dd, J = 4.9, 8.9 Hz, 1H), 7.15 (dt, J = 2.9, 8.4 Hz, 1H), 7.37 (dd, J = 2.9, 9.8 Hz, 1H), 8.60 (s, 1H).EIMS m/z 156 (M + 1).

References

[1] Patent: WO2004/74218, 2004, A2. Location in patent: Page 106
[2] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 43
[3] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 44
[4] Patent: US5514676, 1996, A
[5] Journal of Biological Chemistry, 1954, vol. 207, p. 411,412

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